Translated and Compiled by Rabbi Yair Hoffman for 5tjt.com
1] Who is obligated in paying the shadchan – the chosson’s side or the kallah’s side?
Both sides are obligated to pay the Shadchan for his or her services “Dmai Shadchanus.”
2] What if we are dealing with an unsolicited shadchan?
Even when the Shadchan involved himself of his own accord, without having been requested to do so, if the Shidduch comes about he must be paid the full amount.
3] What is the halacha regarding timing of the payment to the Shadchan?
The timing of the payment is dependent upon the local custom. Nowadays, the custom is to make payment at the time of the Vort or of the T’naim. It is forbidden to delay payment. Therefore, it is incumbent upon both sides to pay the shadchanus immediately after the T’naim.
4] Let’s say it got delayed. Are there issurim involved?
If the time passed and the Shadchan was not paid, there is a violation of Bal Salin and a negation of Bayomo titian s’charo.
5] What if the shadchan suggested the shidduch on Shabbos and did no other work during the week?
If the Shadchan suggested the Shidduch on Shabbos, and he did no further activity during the week, even though it is permitted to engage in Shidduchim on Shabbos, he is not permitted to be compensated for his activities because this is considered Schar Shabbos.
6. What is the halacha when there are two shadchanim?
If two Shadchanim brought together a shidduch to fruition – if one of them suggested the idea and the other actually carried it out, the custom is that the one who presented the idea receives one third, while the one who carried it out receives two thirds. However, all this follows the custom of the place.
7. What if the shadchan is resuggesting a shidduch that was suggested before?
If a Shidduch was presented to two sides, and one side agreed to the shidduch, but the other side paid no heed to the suggestion, and after a number of months someone else came and stated that it is possible that the other side will now consider the suggestion – that person is now to be considered as the one who suggested the shidduch in regard to payment of Shadchanus.
8. What if the shadchan was moichel from one side?
If a Shadchan forwent one side’s share of the Shadchanus, the other side is still obligated in paying their half.
9. Let’s say an American suggested a shidduch for an Eretz Yisroel couple?
When there is a price differential between the rate of Shadchanus in Israel and outside of Israel, the Shadchanus is established based upon where the Chosson and Kallah are living, even if the Shadchan is from another country.
10. What is the halacha when the shadchan is a relative?
If the Shadchan is a family member, he or she must still be paid the same going price as other Shadchanim. If one of the parents himself or herself was the Shadchan, the other side has no obligation to pay the price of Shadchanus.
11. Do the same guidelies apply for a Sefardic shadchan?
It is the custom of most Sefardic communities not to pay a Shadchan fee.
12. What if the bride and groom are both Ashkenazim?
If the Shadchan is of Sefardic background and the bride and groom are from an Ashkeazic background, they must pay the Shadchan fee, for everything follows the bride and the groom.
13. What if the Shadchan is Ashkenaic but the bride and groom are Sefardic?
If the Shadchan is of Ashkenazic background and the bride and groom are of Sefardic background that are not accustomed to pay a Shadchan fee, he does not receive payment of the Shadchan fee, for since it is not their custom to pay for this, he did not work on the condition that he be paid.
The above has been taken from the works of Reb Lipa Israelson – shlita